Home > Name List By other > (3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4, 5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3, 4-c]pyran-8-o... Germany

CAS No 20831-76-9 , (3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,
5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,
4-c]pyran-8-one Search by region : Germany

  • Name: (3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,
    5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,
    4-c]pyran-8-one
  • Synonyms: SureCN154304; MEGxp0_000872; MLS002473254;Gentiopicrin; HMS2198G10; CHEMBL508320; AC1L3GBF; ACon1_001284; 20831-76-9;(3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,
    5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,
    4-c]pyran-8-one;
  • CAS Registry Number:
  • Melting Point: 191 ºC
  • Density: 1.52 g/cm3
  • Refractive index: 1.623
  • Alpha: -200 º (C=2, H2O)
  • EINECS: 244-070-2
  • Molecular Weight: 356.3246
  • InchiKey: DUAGQYUORDTXOR-GPQRQXLASA-N
  • InChI: InChI=1S/C16H20O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)
    11(18)10(5-17)24-16/h2-3,6-7,10-13,15-20H,1,4-5H2/t7-,10-,11-,12+,13-,
    15+,16+/m1/s1
  • Molecular Formula: C16H20O9
  • Molecular Structure:CAS No:20831-76-9 (3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,<br />5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,<br />4-c]pyran-8-one

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1/1
References of (3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,
5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,
4-c]pyran-8-one
Title: Gentiopicrin
CAS Registry Number: 20831-76-9
CAS Name: (5R-trans)-5-Ethenyl-6-(b-D-glucopyranosyloxy)-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one
Synonyms: gentiopicroside
Molecular Formula: C16H20O9
Molecular Weight: 356.32
Percent Composition: C 53.93%, H 5.66%, O 40.41%
Literature References: The principal bitter glucoside of common gentians, which was isolated in 1862 from Gentiana lutea, L., Gentianaceae: Canonica et al., Tetrahedron 16, 192 (1961). Isoln from roots of G. lutea: Korte, Ber. 87, 512 (1954); Korte et al., ibid. 91, 759 (1958). Structure: Canonica et al., Tetrahedron Lett. 1960(24), 7; Tetrahedron 16, 192 (1961). Revised structure: Inouye et al., Tetrahedron Lett. 1968, 4429. Absolute configuration: Manitto, Pagnoni, Gazz. Chim. Ital. 94, 229 (1964).
Properties: Crystals from anhydr ethyl acetate or abs alcohol, mp 191°. [a]D20 -199° (ethanol). uv max (c = 0.0285 g/l methanol): 270 nm (log e 3.96).
Melting point: mp 191°
Optical Rotation: [a]D20 -199° (ethanol)
Absorption maximum: uv max (c = 0.0285 g/l methanol): 270 nm (log e 3.96)
 
Derivative Type: Hemihydrate
Properties: Crystals from 50% ethanol, mp 121°.
Melting point: mp 121°
 
Derivative Type: Tetraacetate
Molecular Formula: C24H28O13
Molecular Weight: 524.47
Percent Composition: C 54.96%, H 5.38%, O 39.66%
Properties: Crystals from methanol. mp 138.5-139.5°. uv max (c = 0.0214 g/l methanol): 272 nm (log e 3.84).
Melting point: mp 138.5-139.5°
Absorption maximum: uv max (c = 0.0214 g/l methanol): 272 nm (log e 3.84)
 
Therap-Cat: Antimalarial.
Keywords: Antimalarial.